Insurance Upskill | Masterclasses

Communication, Cognitive Skills & Professional Effectiveness

Alongside our specialist English, Spanish and Portuguese language academies for insurance professionals, Insurance Upskill offers a complementary suite of masterclasses in communication, behavioural psychology, critical thinking and workplace effectiveness.

Designed for insurance and financial services professionals, these practical sessions help participants communicate with clarity, strengthen client relationships, exercise sound judgement and apply new techniques immediately at work.

The INSURE critical-thinking model and the SURE customer-understanding model were developed specifically for the insurance industry by our founder, Jeff Heasman.

Each masterclass is available as a 1-, 2- or 3-hour session, online or face to face. Choose one session or combine several to create a tailored programme.

Communication, Influence & Persuasion

5¾ Psychology Tips That Will Boost Your Powers of Persuasion

Discover how small psychological insights can make a significant difference to your ability to influence decisions, gain agreement and communicate more persuasively.

5 Communication Habits of Highly Effective Insurance & Financial Services Professionals

Explore five practical communication habits that strengthen relationships, reduce misunderstandings and improve professional effectiveness.

From Death by PowerPoint to Calls to Adventure That Win Business: Presentation Skills for Insurance & Financial Services Professionals

Transform information-heavy slides into engaging presentations that capture attention, communicate value and inspire action.

5 Ways to Improve the Way You Use & Ask Questions Throughout the Customer Journey

Learn how better questions uncover client needs, challenge assumptions, clarify expectations and create more meaningful conversations.

Powers of Persuasion: Top Tips for Persuasive Writing

Discover how to structure written communications that engage readers, strengthen arguments and encourage positive responses.

The 7 Principles of Influence & Persuasion and How They Win Business

Explore psychological principles that influence decisions and learn how to apply them ethically in commercial relationships.

Storytelling: Communicate With Power and Transform Your Business

Use storytelling to make complex information memorable, connect with audiences and communicate with greater impact.

Critical Thinking, Cognitive Skills & Decision-Making

The Proof Gap: Why Statements, Facts, Data, and Evidence Are Not the Same

Explore the differences between information, evidence and proof, and why confusing them can lead to flawed judgements.

Who's Doing the Thinking? Cognitive Offloading and Critical Thinking in the AI Age

Discover how to retain independent judgement, challenge automated outputs and avoid excessive reliance on AI.

Cognitive Flexibility: An Essential Skill for the Modern Insurance Workplace

Adapt your thinking, challenge assumptions and respond effectively to changing circumstances and unfamiliar problems.

Critical Ignoring: A Key Skill to Work Effectively and Advise Clients in a Digital and Information Economy

Learn why knowing what to ignore is as important as knowing what to focus on in an information-rich workplace.

Critical Thinking & Decision-Making Skills: The INSURE Model

Use the founder-developed INSURE model to question assumptions, evaluate evidence and make sound insurance decisions.

Groupthink: What Is It and Why Is It So Important to Deal With It?

Explore how pressure for agreement undermines team decisions and how to encourage constructive challenge.

Human vs. Automated Decision-Making: Have We Gone Too Far?

Consider where automation adds value and where human judgement, accountability and oversight remain essential.

The Art of Disagreement

Challenge ideas and express alternative perspectives constructively without damaging relationships.

Customer Psychology, Behaviour & Understanding

Behavioural Biases in the Customer Journey: How to Identify and Handle Them to Avoid Customer Harm

Recognise how cognitive biases affect customer choices and support informed decisions and fair outcomes.

Customer Decisions: What Psychology & Behavioural Economics Can Teach Us

Understand why customers do not always decide rationally and how to communicate products, options and advice more effectively.

SURE: A New Technique to Ensure Clients Have Understood Your Advice

Go beyond asking whether clients understand: use the founder-developed SURE model to identify misunderstandings.

How to Understand and Explain Insurance Policies in 5 Easy Steps

Interpret complex policy wording and explain coverage, exclusions and conditions in accessible language.

Relationships, Listening & Human Connection

The Social Brain: Building and Maintaining Human Relationships

Explore what neuroscience teaches us about trust, connection and lasting professional relationships.

How to Create Curiosity

Use curiosity to open conversations, challenge assumptions and uncover useful information.

The Art of Effective Listening and Connecting With People

Develop listening techniques that demonstrate understanding, build rapport and encourage openness.

Humanising Communication & Increasing Client Interaction in an Automated World

Preserve empathy and meaningful client relationships as digital technology reshapes insurance interactions.

The Art of Listening to What People Don't Say

Recognise unspoken concerns and use thoughtful questions to understand what may be missing from conversations.

Diversity in Communication: How to Communicate With a Wider and More Diverse Audience

Adapt communication to different experiences, expectations and preferences to improve inclusion and understanding.

Difficult Conversations, Objections & Complaints

Communicating With Customers in Difficult and Uncertain Times

Acknowledge concerns, manage expectations and maintain confidence during challenging circumstances.

From Criticism to Collaboration: Communication Strategies for Resolving Complaints

Reduce defensiveness and turn complaints into constructive conversations focused on resolution.

Hard Talk: Handling Client Objections in Tough Market Conditions

Respond confidently to resistance and difficult questions while preserving productive client relationships.

Professional Writing, Reporting & Workplace Effectiveness

5 Ways to Transform the Way You Write Reports

Make reports clearer, more concise and more useful, with key analysis and recommendations easy to find.

Meetings: Making More of Less

Improve preparation, participation and decision-making to make meetings shorter and more productive.

Writing to Express and Not to Impress: Plain Language for Insurance and Financial Services Professionals

Replace jargon and unnecessary complexity with clear, confident writing that helps readers act.

Choose Your Session Length

Every masterclass can be booked as a one, two or three hour session. Select your preferred length and book your time directly through Calendly.

1 hour

Masterclass

A focused one-hour masterclass session with Jeff, booked directly through Calendly at a time that suits you.

2 hours

Masterclass

A two-hour masterclass session with Jeff, giving more time to explore the topic in depth. Booked directly through Calendly.

3 hours

Masterclass

The full three-hour masterclass session with Jeff, for the most comprehensive coverage of the topic. Booked directly through Calendly.

Not Sure Which Masterclass You Need?

Book a 30-minute introductory meeting with Jeff to talk through your needs first, and he will help you choose the right masterclass and session length for you or your team.